91525-98-3

Upstream product

• 124-70-9 Dichloromethylvinylsilane 
• 299-42-3 (R,R)-(-)-pseudoephedrine 
• 299-42-3 ephedrine 
• 74-88-4 methyl iodide 
• 492-41-1 (1R,2S)-norephedrine 
• 77387-33-8 (1R,2S)-(-)-N-formylnorephedrine 

Downstream Products

• 91525-91-6 N,N'-Bis-((1R,2S)-2-methoxy-1-methyl-2-phenyl-ethyl)-Si,N,N'-trimethyl-Si-vinyl-silanediamine 
• 144760-34-9 cinnamyldimethyl-<1'-(R)-methyl-2'-(S)-phenyl-2-methoxyethyl-N-methylaminomethyl>silane 
• 91525-94-9 C₂₉H₄₇BrMgN₂O₂Si 

Relevant academic research and scientific papers

O-Methylephedrine: A versatile and highly efficient ortho-directing group. Synthesis of enantiopure 1,2-disubstituted ferrocene derivatives

O-Methylephedrine was identified as a very efficient chiral auxiliary for ortho-lithiation reactions of ferrocenes. (1R,2S)-O-Methylephedrine [CH3NHCH(CH3)CH(Ph)OCH3] was reacted with N-ferrocenylmethyl-N,N,N-trimethylammo

Regio-, Stereo-, and Enantioselectivity in the Electrophilic Reactions of 2-Amino-4-phenyl-3-butenenitriles

The allylic anion generated from 2-(N-methylanilino)-4-phenyl-3-butenenitrile (1) reacted with iodomethane and 3-bromo-1-chloropropane in THF/HMPA to give γ-substituted products exclusively, predominantly in the 2Z-configuration.Substitution of the N-methylanilino group with the methyl ether of L-(-)-ephedrine resulted in the generation of chiral aminonitrile 2.Lithiated 2 reacted sluggishly in THF with allyl bromide and benzyl chloride in the absence of HMPA to give the γ-substituted products predominantly in the 2Z-configuration, with little diastereoselectivity.The aminonitrile 3 prepared from cinnamaldehyde, L-(-)-ephedrine, and KCN was lithiated with 2 equiv of LDA resulting in high facial selectivity (76 - 100 percent diastereomeric excess) in alkylations in the presence of HMPA and LiI.Lithiated 3 reacted with propionaldehyde, benzaldehyde, and p-bromobenzaldehyde at -78 deg C to give the γ-addition products, predominantly in the 4R-configuration (64 -78 percent de).The stereochemistry of the isomers of each product was determined by chemical correlation and spectral methods including analyses of the CD spectra and X-ray diffraction.A bicyclic transition state C wherein lithium is chelated by both amino and alkoxy groups is proposed to interpret the observed stereoselectivity.

CHIRAL CATALYSIS IN THE ALKYLATION OF ALDEHYDES WITH DIETHYL ZINC

The reaction of diethyl zinc with benzaldehyde and ephedrine derived catalyst was investigated.It was found that O-alkylated ephedrine could act as a catalyst for the reaction, but that the reaction was no longer stereoselective to the same degree as for the ephedrine catalysed reaction.

ASYMMETRIC SYNTHESIS VIA CHIRAL SILICON REAGENTS. CHIRAL α-HYDROXYALKYL ANION EQUIVALENTS FROM VINYLSILANES CONTAINING OPTICALLY ACTIVE AMINO OR ALKOXY GROUPS ON SILICON

Chiral vinylsilanes containing optically active functional groups on silicon have been used as precursors for chiral α-hydroxyalkyl anion equivalents via a sequence of addition of n-butyllithium, coupling with organic halides, and oxidative cleavage of the silicon-carbon bond, to give optically active alcohols of up to 60percent ee.